Synthesis of (±)-merrilactone A and (±)-anislactone A

Lei Shi; Karsten Meyer; Michael F. Greaney

doi:10.1002/anie.201005156

Synthesis of (±)-merrilactone A and (±)-anislactone A

Lei Shi, Karsten Meyer, Michael F. Greaney

Research output: Contribution to journal › Article › peer-review

Abstract

A concise synthesis of each of the sesquiterpenoids merrilactone A and anislactone A is described using a common route. Reductive cleavage of an epoxide using TiIII and radical cyclization is used to install the C9 quaternary center at the heart of the BC bicycle (see scheme). Selective lactonization sequences then define regiodivergent pathways to both merrilactone A (formal synthesis) and anislactone A (total synthesis). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	9250-9253
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	48
DOIs	https://doi.org/10.1002/anie.201005156
Publication status	Published - 22 Nov 2010

Keywords

diastereoselectivity
natural products
terpenoids
total synthesis

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10.1002/anie.201005156

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title = "Synthesis of (±)-merrilactone A and (±)-anislactone A",

abstract = "A concise synthesis of each of the sesquiterpenoids merrilactone A and anislactone A is described using a common route. Reductive cleavage of an epoxide using TiIII and radical cyclization is used to install the C9 quaternary center at the heart of the BC bicycle (see scheme). Selective lactonization sequences then define regiodivergent pathways to both merrilactone A (formal synthesis) and anislactone A (total synthesis). Copyright {\textcopyright} 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "diastereoselectivity, natural products, terpenoids, total synthesis",

author = "Lei Shi and Karsten Meyer and Greaney, {Michael F.}",

note = "CAPLUS AN 2010:1440303(Journal)",

year = "2010",

month = nov,

day = "22",

doi = "10.1002/anie.201005156",

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volume = "49",

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journal = "Angewandte Chemie - International Edition",

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T1 - Synthesis of (±)-merrilactone A and (±)-anislactone A

AU - Shi, Lei

AU - Meyer, Karsten

AU - Greaney, Michael F.

N1 - CAPLUS AN 2010:1440303(Journal)

PY - 2010/11/22

Y1 - 2010/11/22

N2 - A concise synthesis of each of the sesquiterpenoids merrilactone A and anislactone A is described using a common route. Reductive cleavage of an epoxide using TiIII and radical cyclization is used to install the C9 quaternary center at the heart of the BC bicycle (see scheme). Selective lactonization sequences then define regiodivergent pathways to both merrilactone A (formal synthesis) and anislactone A (total synthesis). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - A concise synthesis of each of the sesquiterpenoids merrilactone A and anislactone A is described using a common route. Reductive cleavage of an epoxide using TiIII and radical cyclization is used to install the C9 quaternary center at the heart of the BC bicycle (see scheme). Selective lactonization sequences then define regiodivergent pathways to both merrilactone A (formal synthesis) and anislactone A (total synthesis). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - diastereoselectivity

KW - natural products

KW - terpenoids

KW - total synthesis

U2 - 10.1002/anie.201005156

DO - 10.1002/anie.201005156

M3 - Article

SN - 1433-7851

VL - 49

SP - 9250

EP - 9253

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 48

ER -

Synthesis of (±)-merrilactone A and (±)-anislactone A

Abstract

Keywords

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